Hydrosilation in high boiling natural vegetable oils

a technology of natural vegetable oil and hydrosilation, applied in the field of hydrosilation, can solve the problems of surfactant performance, additional manufacturing problems, and disadvantages of use, and achieve the effects of improving compression sets, good results, and moderated reaction exotherm

Inactive Publication Date: 2000-06-06
GENERAL ELECTRIC CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

By conducting the hydrosilation reaction in the manner indicated above, and employing the high boiling point natural vegetable oils, improvements arc obtained in aspects of the reaction, such as reaction rate, reaction yield, reaction selectivity, reaction processing during manufacture or reaction product processing in polyurethane foam, personal care and coatings applications. For example, when at least 20 weight percent (based on the total weight of reactants) soybean oil is used, it aids in the handling of the reactants

Problems solved by technology

In the majority of the aforementioned processes, the hydrocarbon solvent is removed after the hydrosilation reaction is completed, since in most cases, the solvent is too flammable, toxic or otherwise detrimental to the final product or further processing steps in which the copolymer is utilized.
However, disadvantages attend their use.
Such disadvantages include: (A) IPA competes with the unsaturated polyether for the silanic sites (SiH) on the siloxane backbone resulting in the formation of the isopropoxysilyl, (CH.sub.3).sub.2 CHOSi, functional group which reduces surfactant performance in urethane foam; (B) IPA reacts with isocyanate in polyurethane foam formulations effectively lowering the isocyanate index of the formulation, so that the IPA must be stripped from the product and recovered, a process which is both time consuming and expensive; (C) IPA is miscible with water which is harmful in the manufacture of polyurethane foam surfactants; and (D) toluene and IPA are flammable which creates additional manufacturing problems.
In addition, prolonged stripping of surfactants manufacture

Method used

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Examples

Experimental program
Comparison scheme
Effect test

examples 1-6

are comparative examples in which known hydrosilation reaction solvents currently used in the preparation of siloxane-oxyalkylene or siloxane-alkyl copolymers were employed. The illustrated aromatic solvents include toluene and Ucane Alkylate-11.TM. (available from Union Carbide Corp.), which are known to those skilled in the art of hydrosilation chemistry. These examples demonstrate the less than desired hydrosilation reaction compatibility characteristics of the solvent and / or the highly volatile nature of the resulting product. Examples 7-21 below demonstrate the production of copolymers in higher boiling point natural vegetable oil solvents including soybean oil (Examples 7-16), linseed oil (Examples 17-20) and safflower oil (Example 21) as examples of the present invention with improved hydrosilation reaction characteristics and reduced product volatility without removal of the reaction solvent from the resulting surfactant product.

In addition to the SiH test for reaction compl...

example 7

A well stirred mixture of 23.72 grams of 1-octene, 36.28 grams of an organohydrogen-polysiloxane of formula, MD'M, and 240 grams (80 wt %) of soybean oil was dcaerated by nitrogen sparge and heated to 75.degree. C. A solution of H.sub.2 PtCl.sub.6.6H.sub.2 O in ethanol was added to the mixture in sufficient amount to provide 20 ppm Pt. The heat source was removed and the exothermic hydrosilation reaction was allowed to proceed until no further temperature increase was noted. Heat was then added to the mixture as needed to keep its temperature at 75.degree. C. for 2 hours. Care was taken never to allow the reaction pot to exceed 100.degree. C. A clear solution of a siloxane-alkyl copolymer with no residual silanic hydrogen content and a 25.degree. C. viscosity of 29 cSt was obtained.

example 8

A well stirred mixture of 166.4 grams of Polyether B ,33.8 grams of an organohydrogen polysiloxane of average formula MD'M and 200 grams (50 wt %) of soybean oil was deacrated by nitrogen sparge and heated to 75.degree. C. A solution of H.sub.2 PtCl.sub.6.6H.sub.2 O in ethanol was added to the mixture in sufficient amount to provide 20 ppm Pt. The heat source was removed and the exothermic hydrosilation reaction was allowed to proceed until no further temperature increase was noted. Heat was then added to the mixture as needed to keep its temperature at 75.degree. C. for 2 hours. Care was taken never to allow the reaction pot to exceed 100.degree. C. A clear solution of a siloxane-oxyalkylene copolymer containing no detectable levels of residual silanic hydrogen and showing a 25.degree. C. viscosity of 64 cSt was obtained.

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Abstract

An improved process is provided for the preparation of siloxane-oxyalkylene and siloxane-alkyl copolymer compositions via a hydrosilation reaction in the presence of high boiling point natural vegetable oils as the reaction solvent. The reaction solvent need not be removed from the block copolymer product, and indeed is beneficial to remain with the copolymer particularly when the copolymer is used as a surfactant for polyurethane foam formulations. Soybean oil and linseed oil are the preferred high boiling natural oil solvents when the copolymer product is to be used in the preparation of the surfactants for polyurethane foams. High resiliency polyurethane foam prepared with these natural oils present in the surfactant preparation afforded improved compression sets, wet compression sets and humid aged compression sets. Additionally, the use of the surfactants made with natural oils as a reaction solvent or consequently surfactants post diluted with natural oils when employed in the preparation of polyurethane foam afforded foams with greatly reduced amounts of "glass fogging".

Description

This invention relates in general to an improved process for the preparation of organopolysiloxane surfactants. In one aspect, this invention is directed to a process for the preparation of improved siloxanc-oxyalkylene copolymer compositions. In a further aspect, the invention is directed to siloxane-oxyalkylene and siloxane-alkyl copolymers and organosiloxanes that are suitable for use as surfactants in, for instance, polyurethane foam, coatings applications, or personal care products.The preparation of siloxane-oxyalkylence or siloxane-alkyl copolymers by the hydrosilation reaction of an organohydrogen siloxane and an unsaturated olefin hydrocarbon or polyoxyalkylene is well known and reported in the literature. The hydrosilation reaction is typically performed in a low molecular weight, highly volatile hydrocarbon solvent such as benzene, toluene or xylene so as to compatibilize the reactants and aid in transfer and filtration of the copolymer products, or to moderate the exothe...

Claims

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Application Information

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IPC IPC(8): C08G77/38C08G77/00C08G77/46C08F283/12C08J9/02C08G18/83C08G77/06C08G77/12C08J9/00C08L83/05
CPCC08G77/38C08G77/46C08J9/0061C08J2491/00C08J2375/04C08G77/08C08J9/04C08G77/14
Inventor AUSTIN, PAUL E.DERDERIAN, EDMOND J.KAYSER, ROBERT A.
Owner GENERAL ELECTRIC CO
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